14811-92-8

Basic information

• Product Name: 3-STEAROYL-SN-GLYCEROL
• Synonyms: 2,3-dihydroxypropylester,(R)-Octadecanoicacid;3-STEAROYL-SN-GLYCEROL;L-ALPHA-STEARIN;(R)-GLYCEROL 1-STEARATE;3-monostearoyl-sn-glycerol;(R)-2,3-dihydroxypropyl stearate;3-STEAROYL-SN-GLYERCOL;(R)-2,3-Dihydroxypropylstearat
• CAS NO: 14811-92-8
• Molecular Formula: C₂₁H₄₂O₄
• Molecular Weight: 358.56
• EINECS: 238-880-5
• Mol File: 14811-92-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 72-73 °C
• Boiling Point: 476.9°Cat760mmHg
• Flash Point: 151.9°C
• Appearance: /
• Density: 0.958g/cm³
• Refractive Index: 1.468
• Storage Temp.: −20°C
• PKA: 13.16±0.20(Predicted)
• CAS DataBase Reference: 3-STEAROYL-SN-GLYCEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-STEAROYL-SN-GLYCEROL(14811-92-8)
• EPA Substance Registry System: 3-STEAROYL-SN-GLYCEROL(14811-92-8)

Safety Data

• WGK Germany: 1
• F: 10
• Hazardous Substances Data: 14811-92-8(Hazardous Substances Data)

Usage

Description

3-Stearoylsn-glycerol, also known as 1,2-diacylglycerol, is a glycerolipid that plays a crucial role in cellular signaling and metabolism. It is composed of a glycerol molecule with two fatty acid chains, specifically stearoyl groups, attached to the first and second carbon atoms. This molecule is involved in various cellular processes, including the regulation of enzyme activity and the synthesis of other lipids.

Uses

Used in Pharmaceutical Applications:
3-Stearoylsn-glycerol is used as a phospholipase A2 inhibitor, which helps in modulating the activity of this enzyme that is involved in the breakdown of membrane phospholipids. The inhibition of phospholipase A2 can have potential therapeutic applications in treating inflammation and other related conditions.
Used in Chemical Synthesis:
3-Stearoylsn-glycerol is used as a precursor in the synthesis of phosphatidylinositol 3,4,5-trisphosphate (PtdIns(3,4,5)P3) and its diastereoisomers. These molecules are essential components of cellular signaling pathways and play a vital role in various cellular processes, such as cell growth, differentiation, and apoptosis.
Used in the Food Industry:
3-Stearoylsn-glycerol can be used as an additive in the food industry due to its emulsifying properties. It helps in stabilizing mixtures of oil and water, which can improve the texture and shelf life of various food products.
Used in Cosmetics:
In the cosmetics industry, 3-Stearoylsn-glycerol can be used as an ingredient in the formulation of creams, lotions, and other skincare products. Its emollient properties help to moisturize and soften the skin, providing a smooth and hydrated feel.
Used in Research:
3-Stearoylsn-glycerol is also used as a research tool in the study of cellular signaling pathways and lipid metabolism. It can be employed in various experimental setups to investigate the role of diacylglycerol in cellular processes and to develop new therapeutic strategies targeting these pathways.

InChI:InChI=1/C21H42O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h20,22-23H,2-19H2,1H3/t20-/m1/s1

Upstream product

• 10567-18-7 (R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-octadecanoate 
• 374591-68-1 (R)-1-O-Stearoyl-2,3-O-(xanthen-9-ylidene)glycerol 
• 57-11-4 stearic acid 
• 112-76-5 Stearoyl chloride 

Downstream Products

• 2177-98-2 1,2-dipalmitoyl-3-stearoyl glycerol 
• 34487-34-8 L-(-)-α-Stearoyl-α'-trityl-glycerin 
• 22610-61-3 (S)-2,3-dihydroxypropyl n-octadecanoate 
• 329327-15-3 1-O-(9-Phenylxanthen-9-yl)-3-O-stearoyl-sn-glycerol 
• 10567-48-3 L-(R)-α-O-Trityl-β,γ-distearoyl-glycerol 
• 329327-16-4 (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (R)-1-octadecanoyloxymethyl-2-(9-phenyl-9H-xanthen-9-yloxy)-ethyl ester 
• 150577-01-8 2-O-Arachidonoyl-3-O-stearoyl-sn-glycerol 
• 65914-84-3 1-stearoyl-2-arachidonoyl-sn-glycerol 
• 2258-95-9 L-(-)-α-Stearoyl-β-linoloyl-α'-trityl-glycerin 
• 621-61-4 glycerol monostearate 
• 10567-18-7 (R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-octadecanoate 

Relevant articles and documents

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Optically active monoacylglycerols: Synthesis and assessment of purity

Despite their simple structures, synthesis of 1(or 3)-acyl-sn-glycerols remains a challenge that cannot be ignored because of facile acyl migrations, which not only complicate the synthesis but also make direct GC or HPLC analysis unfeasible. Assessment of the optical purity of monoacylglycerols has, to date, relied almost exclusively on specific rotation data, which are small in value and thus insensitive to impurities. Now, a simple means to "magnify" the small specific rotations has been found, along with practical methods for the measurement of both 1,2-and 1,3-acyl migrations, which offer a convenient and straightforward alternative to Mori's NMR analysis of Mosher esters. With the aid of these methods, a range of conditions for deacetonide removal were examined en route to the synthesis of two natural monoacylglycerols. Refined hydrolysis conditions, along with useful knowledge about the solubility and reactivity of substrates with an ultra long alkyl chain are also presented. Copyright

Design and synthesis of fluorescence-labeled closo-dodecaborate lipid: Its liposome formation and in vivo imaging targeting of tumors for boron neutron capture therapy

The fluorescence-labeled closo-dodecaborane lipid (FL-SBL) was synthesized from (S)-(+)-1,2-isopropylideneglycerol as a chiral starting material. FL-SBL was readily accumulated into the PEGylated DSPC liposomes prepared from DSPC, CH, and DSPE-PEG-OMe by the post insertion protocol. The boron concentrations and the fluorescent intensities of the FL-SBL-labeled DSPC liposomes increased with the increase of the additive FL-SBL, and the maximum emission wavelength of the liposomes appeared at 531 nm. A preliminary in vivo imaging study of tumor-bearing mice revealed that the FL-SBL-labeled DSPC liposomes were delivered to the tumor tissue but not distributed to hypoxic regions.

Lp-PLA2 inhibitory activities of fatty acid glycerols isolated from Saururus chinensis roots

(R)-Glycerol-monolinoleate 4 and (R)-glycerol-monostearate 5 were isolated from the ethyl acetate extracts of Saururus chinensis roots and (R)- or (S)-fatty acid glycerols 4 and 5 were synthesized for confirming their structures and evaluating their inhibitory activities against Lp-PLA 2. The (R)-4 and (S)-4 exhibited Lp-PLA2 inhibitory activities with IC50 values of 45.0 and 52.0 μM, respectively.